WO2011157651A1 - Dérivés de diamide d'acide anthranilique à chaînes latérales cycliques - Google Patents

Dérivés de diamide d'acide anthranilique à chaînes latérales cycliques Download PDF

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WO2011157651A1
WO2011157651A1 PCT/EP2011/059692 EP2011059692W WO2011157651A1 WO 2011157651 A1 WO2011157651 A1 WO 2011157651A1 EP 2011059692 W EP2011059692 W EP 2011059692W WO 2011157651 A1 WO2011157651 A1 WO 2011157651A1
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alkyl
alkoxy
ring
halogen
spp
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PCT/EP2011/059692
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German (de)
English (en)
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Rüdiger Fischer
Christoph Grondal
Markus Heil
Heinz-Juergen Wroblowsky
Ernst Rudolf Gesing
Arnd Voerste
Ulrich Görgens
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Bayer Cropscience Ag
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Priority to EP11726115.6A priority Critical patent/EP2582695B1/fr
Priority to CN201180038310.7A priority patent/CN103249729B/zh
Priority to KR1020137000990A priority patent/KR20130112864A/ko
Priority to ES11726115.6T priority patent/ES2554903T3/es
Priority to BR112012032238A priority patent/BR112012032238A2/pt
Priority to JP2013514657A priority patent/JP6046035B2/ja
Priority to MX2012014574A priority patent/MX2012014574A/es
Publication of WO2011157651A1 publication Critical patent/WO2011157651A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • the present invention relates to novel Anthranilklarediamid derivatives, their use as insecticides and acaricides for controlling animal pests, also in combination with other agents for increasing the effect, and several processes for their preparation.
  • Anthranilic acid derivatives with insecticidal properties are already described in the literature, e.g.
  • the present invention therefore relates to novel anthranilic diamide derivatives of the formula (I)
  • Ci-C 6 alkyl in which represents hydrogen, amino, hydroxy, or represents in each case optionally monosubstituted or polysubstituted by identical or different substituents
  • Ci-C 6 alkyl C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl, wherein the substituents can be independently selected from halogen, cyano, nitro, hydroxy, C r C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, (dC 4 alkoxy) - carbonyl, Ci-C alkylamino, di (Ci-C alkyl) amino, C 3 -C 6 cycloalkylamino, or (Ci-C alkyl) C 3 - C 6 cycloalkylamino, hydrogen, C r C 6 alkyl, C
  • R 4 is hydrogen, halogen, cyano, nitro, hydroxy, amino, carboxy, OCN, SCN, Ci-C 4 alkyl, C r C 4 - haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl , C 2 -C 6 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 - alkyl, C r C 4 haloalkoxy, SF 5, C 1 -C 4 alkylthio , C 1 -C 4 -alkylthio-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl, CC 4 alkylsulfonyl, Ci-C4-alkylsulfonyloxy, Ci-C4-haloalkylthio, Ci-C4-haloalkylsulfinyl , C
  • n 0 to 3
  • R 5 is -C 6 alkyl, C 3 -C 6 cycloalkyl, C r C 6 haloalkyl, d-Cg-halocycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 - haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, Ci-C 4 alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-alkylsulfinyl, Ci-C 4 alkylsulfonyl, Ci-C 4 haloalkylthio, Ci-C4-haloalkylsulfinyl, Ci-C 4 - haloalkylsulfonyl, halogen, cyano, nitro, or C 3 -C 6 trialkylsilyl group,
  • Qz is a 3- to 4-membered, partially saturated or saturated, or for a 5- to 6-membered, partially saturated, saturated or aromatic ring or is a 6 to 10-membered bicyclic ring system, wherein the ring or the bicyclic Ring system may optionally contain 1 -3 heteroatoms from the series N, S, O, wherein the ring or the bicyclic ring system is optionally mono- or polysubstituted, identically or differently, and wherein the substituents may be independently selected from hydrogen, CrC 6 - alkyl, C 2 -C 6 alkenyl, C 2 -C 6 - alkynyl, C 3 -C 6 cycloalkyl, -C 6 haloalkyl, C 2 -C 6 - Haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN, C0 2 NH 2, N0 2, OH, dC
  • Q is a 5- or 6-membered, partially saturated or saturated heterocyclic or heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, wherein the ring or the ring system, optionally mono- or polysubstituted, identical or different is substituted, said substituents may be independently selected from hydrogen, Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 - C 6 cycloalkyl, dd-haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN, CO 2 H, CO 2 NH 2 , NO 2 , OH, Ci-C 4 alkoxy, Ci -C 4 haloalkoxy, Ci-C4-alkylthio, Ci-C 4 - alkyls
  • R 6 is hydrogen, C r C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C r C 6 haloalkyl, C 2 - C 6 haloalkenyl , C 3 -C 6 -cycloalkoxy or
  • Ci-C 6 alkyl is, independently hydrogen, Ci-C 6 alkyl, C 3 -C 6 cycloalkyl, Ci-C 6 haloalkyl, Halogi cyano, nitro, Ci-C alkoxy, Ci-C -haloalkoxy, Ci-C - Alkylthio or Ci-C haloalkylthio stands,
  • the compounds of formula (I) may optionally be present in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are the subject of the invention and can be used according to the invention.
  • the compounds of formula (I) optionally comprise diastereomers or enantiomers.
  • the compounds of the invention are generally defined by the formula (I). Preferred, particularly preferred and very particular are compounds of the formula (I) in which
  • R 1 preferably represents hydrogen, Ci-C 6 alkyl, C 2 -C 6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, cyano (Ci- Ce-alkyl), C r C 6 -haloalkyl , C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 alkyl, C r C 4 - alkylthio-C 1 -C 4 alkyl, C 1 C 4 alkylsulfinyl-C 1 -C 4 -alkyl or C 1 -C 4 -alkylsulfonyl-C 1 -C 4 -alkyl,
  • R 1 particularly preferably represents hydrogen, methyl, ethyl, cyclopropyl, cyanomethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl,
  • R 1 very particularly preferably represents hydrogen
  • R 2 is preferably hydrogen or C 1 -C 6 -alkyl.
  • R 2 particularly preferably represents hydrogen or methyl.
  • R 2 very particularly preferably represents hydrogen.
  • R 3 preferably represents optionally mono- or polysubstituted, identically or differently substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, where the substituents are selected independently of one another from a saturated or partially saturated heterocyclic ring or an aromatic ring containing no heteroatom, which is optionally monosubstituted or polysubstituted by identical or different substituents with SF 5 , halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, C r C 6 alkyl, C 3 -C 6 cycloalkyl, C r C 4 alkoxy, d-Cg-haloalkyl, C r C 4 haloalkoxy, CC 4 alkylthio, Ci-C 4 alkylsulfinyl, C r C 4 alkylsulf
  • R 3 further preferably represents optionally mono- or polysubstituted, identically or differently substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, where the substituents represent a 5- or 6-membered heteroaromatic ring which is mono- or polysubstituted by identical or different substituents SF 5, halogen, cyano, nitro, hydroxy, amino, carboxy, carbamoyl, dC 6 alkyl, C 3 -C 6 cycloalkyl , C 1 -C 4 alkoxy, dd haloalkyl, C 1 -C 4 -haloalkoxy, CrC 4 alkylthio, Ci-C4-alkylsulfinyl, Ci-C 4 alkylsulfonyl, Ci-d-alkoxycarbonyl, Ci-d- Alky
  • R 3 furthermore very particularly preferably represents optionally mono- or polysubstituted, identically or differently substituted methyl, ethyl, propyl, isopropyl, butyl, sec-butyl and isobutyl, the substituents being selected independently of one another from furan, thiophene, pyrazole , Triazole, hidazole, thiazole, oxazole, isoxazole, isothiazole, thiadiazole, oxadiazole, pyrrole, pyridine, pyrimidine, pyridazine or pyrazine, which are optionally mono- or polysubstituted, identically or differently, by methyl, ethyl, propyl, isopropyl, cyclopropyl , Fluorine, chlorine, bromine, cyano, methoxy, trifluoromethyl, trifluoromethoxy, SF 5 , methylthio, methylsulfon
  • R 3 furthermore very particularly preferably represents substituted phenyl, furan, thiophene, pyrazole, triazole, imidazole, thiazole, oxazole, isoxazole, isothiazole, thiadiazole, oxadiazole, pyrrole, pyridine, pyrimidine, pyridazine or pyrazine, where the substituents are selected independently of one another from methyl, ethyl, propyl, iso.
  • R 3 furthermore very particularly preferably represents substituted aziridine, oxirane, thiirane, azetidine, oxetane, thietane, pyrrolidine, pyrroline, pyrazolidine, pyrazoline, imidazolidine, imidazolidinone, imidazoline, tetrahydrofuran, tetrahydrothiophene, tetrahydrothiophene dioxide, thiazoline, thiazolidine, isothiazolidine, piperidine, piperazine, Hexahydropyridazine, hexahydropyrimidine, tetrahydropyran, dihydrofuranone, dioxane, tetrahydrothiopyran, morpholine, thiomorpholine, thiomorpholino dioxide, azepane, diazepane, oxepan, dioxepane, thiazoline, thiepan,
  • R 4 very particularly preferably represents hydrogen, methyl, trifluoromethyl, cyano, fluorine, chlorine, bromine, iodine or trifluoromethoxy.
  • R 4 particularly preferably represents chlorine or bromine, R 4 furthermore particularly preferably represents iodine or cyano.
  • R 5 is preferably C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 1 -C 9 -halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 - C 4 alkynyl, C 2 -C 4 haloalkynyl, C r C 4 alkoxy, C r C 4 haloalkoxy, C r C 4 - alkylthio, Ci-C4-alkylsulfinyl, Ci-C 4 alkylsulfonyl, Ci- C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, halogen, cyano, nitro or C 3 -C 6 -trial
  • R 5 particularly preferably represents Ci-C4 alkyl, C3-C6-cycloalkyl, Ci-C4-haloalkyl, Ci-C6-halocycloalkyl, C 2 - C 6 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkynyl, Ci-C 4 alkoxy, Ci-C is 4 -haloalkoxy, fluorine, chlorine, bromine, iodine, cyano, nitro, or C 3 -C 6 trialkylsilyl,
  • R 5 very particularly preferably represents methyl, fluorine, chlorine, bromine or iodine, R 5 particularly preferably represents methyl or chlorine
  • a particularly preferably represents CH 2 , CH (CH 3 ), -CH 2 O- or -C ( O) -CH 2 -,
  • Qz preferably represents a 3- to 4-membered, partially saturated or saturated, or for a 5 to 6-membered, partially saturated, saturated or aromatic ring, wherein the ring optionally contains 1-3 heteroatoms from the series N, S, 0 wherein the ring is optionally monosubstituted or polysubstituted by identical or different substituents, and wherein the substituents can be independently selected from hydrogen, C iC 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl , C 3 -C 6 -cycloalkyl, dd-haloalkyl, dd-haloalkenyl, dd-haloalkynyl, dd-halocycloalkyl, halogen, CN, OH, dd-alkoxy, C r C 4 -haloalkoxy, dC 4 -alkylthio, C r C 4 -alkylsulfiny
  • Qz is particularly preferably a 3- to 4-membered, partially saturated or saturated, or a 5-membered, partially saturated, saturated or aromatic ring, said ring optionally containing 1-2 heteroatoms from the series N, S, 0 can wherein the ring is optionally mono- or polysubstituted by identical or different substituents, and wherein the substituents may be independently selected from hydrogen, C iC 6 alkyl, C 2 -C 6 - alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 -cycloalkyl, dC 6 -haloalkyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -haloalkynyl, C 3 -C 6 -halocycloalkyl, halogen, CN, OH, d ⁇ -alkoxy, C r C 4 haloalkoxy, dd alkylthio, C r C 4 alkyl
  • Qz very particularly preferred for azetidine, oxetane or thietane, pyrrolidine, pyrroline, pyrazolidine, pyrazoline, imidazolidine, imidazolidone, imidazoline, tetrahydrofuran, tetrahydrothiophene, thiazolidine, isothiazolidine, isoxazoline, which is optionally monosubstituted or polysubstituted by identical or different substituents, and wherein the substituents may be independently selected from hydrogen, Ci-C 6 alkyl, C 2 -C 6 - alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, dC 6 haloalkyl, C 2 - C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN, OH,
  • R 7 independently of one another are preferably hydrogen, halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylsulfonyl or ( C 4 alkyl) C 1 -C 4 alkoxyimino,
  • R 7 independently of one another particularly preferably C 4 haloalkyl stands for hydrogen, halogen or C r, very particularly preferably represents fluorine, chlorine or bromine, R 7 particularly preferably represents chlorine or bromine, p preferably represents 1, 2 or 3, p particularly preferably represents 1 or 2, p very particularly preferably represents 1,
  • Z is preferably N, CH, CF, CC1, CBr or CI
  • Z particularly preferably represents N, CH, CF, CC1 or CBr,
  • Z very particularly preferably represents N, CC1 or CH
  • R 8 preferably represents linear or branched - (C 1 -C 4 -alkylene) or represents a direct bond
  • R 8 particularly preferably represents methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl or iso-butyl or a direct bond
  • R 8 very particularly preferably represents methyl or ethyl or a direct bond
  • Q preferably represents a 5- or 6-membered, partially saturated or saturated heterocyclic or heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, where the heteroatoms can be selected from the series N, S, O wherein the ring or the ring system is optionally mono- or polysubstituted by identical or different substituents, and wherein the substituents may be independently selected from hydrogen, Ci-C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 C 6 cycloalkyl, C r C 6 - haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN, C0 2 H, C0 2 NH 2, N0 2, OH, dC 4 alkoxy, dC 4 haloalkoxy,
  • Q is particularly preferably an optionally mono- or polysubstituted 5- or 6-membered heteroaromatic ring of the series Ql to Q-53 and Q-58 to Q-59, Q62 to Q63, a is an aromatic 9-membered fused heterobicyclic ring system Q-54 to Q-56 and also a 5-membered heterocyclic ring Q-60 to Q-61, where the substituents can be selected independently of one another from C 1 -C 3 -alkyl, dC 3 - Haloalkyl, dC 2 alkoxy, halogen, cyano, hydroxy, nitro or Ci-C 2 haloalkoxy, or wherein the substituents can be independently selected from phenyl or a 5- or 6-membered heteroaromatic ring, wherein phenyl or the ring optionally singly or multiply, identically or differently with C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C
  • Q is preferably an optionally singly or multiply substituted heteroaromatic ring of the series Q-37, Q-38, Q-39, Q-40, Q43, Q-58, Q-59, Q62 and Q63, and also a 5 heterocyclic ring Q-60, wherein the substituents may be independently selected from chlorine, fluorine, iodine, bromine, cyano, trifluoromethyl and pentafluoroethyl., or wherein the substituents may be independently selected from phenyl or a 5- or 6 -membered heteroaromatic ring, wherein phenyl or the ring is optionally mono- or polysubstituted, identically or differently, with Ci-C ö alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, Ci- C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 --C
  • examples include tetrahydrothiophene dioxide, imidazolidone.
  • the oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
  • lactones and lactams are preferably also included.
  • the oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, for example at N and S, and then form, for example, the divalent groups -N (O) -, -S (O) - (also abbreviated SO) and - S (0) 2 - (also short S0 2 ) in the heterocyclic ring.
  • -N (0) and -S (0) groups both enantiomers are included.
  • Substituents other than the oxo group may also be bonded to a heteroatom on a heterocyclic ring, for example a nitrogen atom, if a hydrogen atom on the nitrogen atom of the main body is replaced. In the case of the nitrogen atom and other heteroatoms such.
  • the sulfur atom is also a further substitution to form quaternary ammonium compounds or sulfonium compounds in question.
  • the compounds of the formula (I) which contain a combination of the meanings given above as being very particularly preferred.
  • the compounds of formulas (I) may be in the form of various regioisomers.
  • Q is the meanings Q62 and Q63, and Q58 and Q59 and the compounds may be in different proportions.
  • the active compounds according to the invention are suitable for plant tolerance, favorable warm-blood toxicity and good environmental compatibility for protecting plants and plant organs, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and molluscs which are found in agriculture, horticulture, livestock, forests, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Anoplura e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.
  • arachnids e.g. Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp.
  • Eriophyes spp. Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp. Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.
  • Diabrotica spp. Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochlear iae
  • Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp. From the order of the Collembola eg Onychiurus armatus. From the order of the Dermaptera eg Forficula auricularia. From the order of Diplopoda eg Blaniulus guttulatus.
  • Gastropoda e.g. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomel
  • helminths e.g. Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Ne
  • protozoa such as Eimeria
  • Eimeria protozoa
  • Heliopeltis spp. Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodnius spp. Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.
  • Laodelphax striatellus Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis p ecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praeonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp.,
  • Saissetia spp. Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii. From the order of Hymenoptera eg Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Lepidoptera From the order of Lepidoptera, for example, Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia dandana, Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp.
  • Plutella xylostella Prodenia spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp.
  • Orthoptera e.g. Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
  • siphonaptera e.g. Ceratophyllus spp., Xenopsylla cheopis.
  • Symphyla e.g. Scutigerella immaculata.
  • Thysanoptera e.g. Basothrips biformis, Enneothrips hevens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.
  • Thysanura e.g. Lepisma saccharina.
  • the plant parasitic nematodes include e.g. Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp.
  • Trichodorus spp. Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.
  • the effectiveness of the compounds of formula (I) can be increased by the addition of ammonium and phosphonium salts.
  • the ammonium and phosphonium salts are defined by formula (XI)
  • D is nitrogen or phosphorus, D is preferably nitrogen,
  • R 10 , R 11 , R 12 , and R 13 independently of one another represent hydrogen or in each case optionally substituted C 1 -C 8 -alkyl or mono- or polyunsaturated, optionally substituted C 1 -C 8 -alkylene, the substituents being halogen, nitro and Cyano can be selected R 10 , R 11 , R 12 , and R 13 preferably independently of one another represent hydrogen or in each case optionally substituted C 1 -C 4 -alkyl, where the substituents can be selected from halogen, nitro and cyano,
  • R 10 , R 11 , R 12 , and R 13 more preferably independently of one another represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl or t-butyl,
  • R 10 , R 11 , R 12 , and R 13 are very particularly preferably hydrogen, m is 1, 2, 3 or 4, m is preferably 1 or 2,
  • R 14 is an inorganic or organic anion
  • R 14 b preferably comprises hydrogencarbonate, tetraborate, fluoride, bromide, iodide, chloride, monohydrogenphosphate, dihydrogenphosphate, hydrogensulphate, tartrate, sulphate, nitrate, thiosulphate, thiocyanate, formate, lactate, acetate, propionate, butyrate, pentanoate, citrate or oxalate stands,
  • R 14 is particularly preferred for lactate, sulfate, monohydrogen phosphate, dihydrogen phosphate, nitrate, thiosulfate, thiocyanate, citrate, oxalate or formate.
  • R 14 very particularly preferably represents sulfate.
  • the ammonium and phosphonium salts of the formula (XI) can be used in a wide concentration range for increasing the effect of crop protection agents containing compounds of the formula (I).
  • the ammonium or phosphonium salts are used in the ready-to-use crop protection agent in a concentration of 0.5 to 80 mmol / l, preferably 0.75 to 37.5 mmol / l, more preferably 1, 5 to 25 mmol / l.
  • the ammonium and / or phosphonium salt concentration in the formulation is selected to be in the specified general, preferred or most preferred ranges after dilution of the formulation to the desired drug concentration.
  • the concentration of the salt in the formulation is usually 1-50 wt .-%.
  • a penetration promoter is added to the crop protection agents to increase the effect. Even in these cases, an increase in activity can be observed.
  • the present invention is therefore also the use of a penetration promoter, as well as the use of a Combination of penetration enhancer and ammonium and / or phosphonium salts to increase the efficacy of pesticides containing acaricidal / insecticidal compounds of the formula (I) as an active ingredient.
  • the subject matter of the invention is the use of these agents for controlling harmful insects.
  • Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
  • penetration promoters are defined by the fact that they can penetrate from the aqueous spray mixture and / or from the spray coating into the cuticle of the plant and thereby increase the material mobility (mobility) of active substances in the cuticle.
  • the method described in the literature can be used to determine this property.
  • Suitable penetration promoters are, for example, alkanol alkoxylates.
  • Penetration promoters according to the invention are alkanol alkoxylates of the formula
  • R is straight-chain or branched alkyl having 4 to 20 carbon atoms
  • R ' is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl or n-hexyl,
  • AO stands for an ethylene oxide radical, a propylene oxide radical, a butylene oxide radical or mixtures of ethylene oxide and propylene oxide radicals or butylene oxide radicals and v stands for numbers from 2 to 30.
  • a preferred group of penetration enhancers are alkanol alkoxylates of the formula
  • R ' has the meaning given above, EO stands for -CH 2 -CH 2 -0- and n stands for numbers from 2 to 20.
  • Another preferred group of penetration enhancers are alkanol alkoxylates of the formula R-O - (- EO-) p - (- PO-) q -R '(XH-b) in which
  • R has the abovementioned meaning, R 'has the abovementioned meaning, EO stands for -CH 2 -CH 2 -O-,
  • PO is CH-CH-0 ;
  • CH 3 p is a number from 1 to 10 and q is a number from 1 to 10.
  • Another preferred group of penetration enhancers are alkanol alkoxylates of the formula R-0 - (- PO-) r - (EO-) s -R '(XII-c) in which R has the meaning given above, R' is the one given above Meaning, EO stands for -CH 2 -CH 2 -0-,
  • CH 3 r stands for numbers from 1 to 10 and s stands for numbers from 1 to 10.
  • alkanol alkoxylates of the formula R-0 - (- EO-) p - (- BO-) q -R '(XH-d) in which
  • R and R have the meanings given above, EO is CH 2 -CH 2 -O-,
  • BO is - CH CH-CH-0
  • CH 3 p is a number from 1 to 10 and q is a number from 1 to 10.
  • Another preferred group of penetration enhancers are alkanol alkoxylates of the formula R-O - (- BO-) r - (- EO-) s -R '(XH-e) in which
  • BO is - CH CH-CH-0
  • EO is CH 2 -CH 2 -O-, r is a number from 1 to 10 and s is a number from 1 to 10.
  • alkanol alkoxylates of the formula CH 3 - (CH 2 ) t -CH 2 -O - (- CH 2 -CH 2 -O-) u -R '(XII-f) in which
  • R ' has the meaning given above, t represents numbers from 8 to 13, u represents numbers from 6 to 17.
  • R is preferably butyl, isobutyl, n-pentyl, i-pentyl, neopentyl, n-hexyl, i-hexyl, n-octyl, i-octyl, 2-ethylhexyl, nonyl, i-nonyl, decyl, n Dodecyl, i-dodecyl, lauryl, myristyl, i-tridecyl, trimethyl-nonyl, palmityl, stearyl or eicosyl.
  • alkanol alkoxylate of the formula (XII-c) is 2-ethyl-hexyl alkoxylate of the formula
  • EO stands for -CH 2 -CH 2 -0-
  • EO is CH 2 -CH 2 -O-
  • BO is - CH-CH-CH-0
  • CH 3 the numbers 10, 6 and 2 average values, called.
  • alkanol alkoxylates of the formula (XII-f) are compounds of this formula in which t is from 9 to 12 and u is from 7 to 9.
  • alkanol alkoxylate of the formula (XII-f-1) CH 3 - (CH 2 ) t -CH 2 -O - (- CH 2 -CH 2 -O-) u -R '(XII-f -1) in which t stands for the average value 10.5 and u stands for the average value 8.4.
  • the alkanol alkoxylates are generally defined by the above formulas. These substances are mixtures of substances of the specified type with different chain lengths. For the indices, therefore, average values are calculated, which can also differ from whole numbers.
  • the alkanol alkoxylates of the formulas given are known and are partly available commercially or can be prepared by known methods (compare WO 98/35 553, WO 00/35 278 and EP-A 0 681 865).
  • Suitable penetration promoters are substances which promote the solubility of the compounds of the formula (I) in the spray coating. These include, for example, mineral or vegetable oils. Suitable oils are all mineral or vegetable, optionally modified, oils which can usually be used in agrochemical compositions. Examples include sunflower oil, rapeseed oil, olive oil, castor oil, rapeseed oil, corn kernel oil, cottonseed oil and soybean oil or the esters of said oils. Rape oil, sunflower oil and their methyl or ethyl esters are preferred.
  • the concentration of penetration promoter can be varied within a wide range. In the case of a formulated crop protection agent, it is generally from 1 to 95% by weight, preferably from 1 to 55% by weight, more preferably from 15 to 40% by weight.
  • the concentration is generally between 0.1 and 10 g / l, preferably between 0.5 and 5 g / l.
  • Combinations of active ingredient, salt and penetration enhancer highlighted in accordance with the invention are listed in the following table: "According to the test” means that any compound which is suitable in the test for penetration of the cuticle (Baur et al., 1997, Pesticide Science 51, 131-152 ) acts as a penetration promoter:
  • the compounds according to the invention may also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as anti-MLO agents ( Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural products, active ingredient Impregnated synthetic materials, fertilizers and Feinstverkapselitch in polymeric materials.
  • solutions emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural products, active ingredient Impregnated synthetic materials, fertilizers and Feinstverkapselitch in polymeric materials.
  • formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders ie liquid solvents and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
  • Excipients which can be used are those which are suitable for imparting special properties to the composition itself and / or preparations derived therefrom (for example spray liquor, seed dressing), such as certain technical properties and / or specific biological properties.
  • Typical auxiliaries are: extenders, solvents and carriers.
  • Suitable extenders include, for example, water, polar and non-polar organic chemical liquids, for example from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or este
  • organic solvents can also be used as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg petroleum fractions, mineral and vegetable oils , Alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulfoxide, and water.
  • Suitable solid carriers are: e.g. Ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates, as solid carriers for granules are suitable: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates;
  • suitable dispersants are non-ionic and / or ionic substances, e.g.
  • POE and / or POP ethers from the classes of alcohol POE and / or POP ethers, acid and / or POP-POE esters, alkyl-aryl and / or POP-POE ethers, fatty and / or POP-POE adducts, POE and / or POP polyol derivatives, POE and / or POP sorbitol or sugar adducts, alkyl or aryl sulfates, sulfonates and phosphates or the corresponding PO ether adducts.
  • suitable oligo- or polymers e.g. starting from vinylic monomers, from acrylic acid, from EO and / or PO alone or in combination with e.g.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations.
  • Dyes such as inorganic pigments such as iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • Other additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present.
  • the formulations generally contain between 0.01 and 98% by weight of active ingredient, preferably between 0.5 and 90%.
  • the active ingredient according to the invention may be present in its commercial formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or semiochemicals.
  • active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or semiochemicals.
  • a mixture with other known active substances, such as herbicides, fertilizers, growth regulators, safeners, semiochemicals, or with agents for improving the plant properties is possible.
  • the active compounds according to the invention may also be present in the form of insecticides in their commercial formulations and in the forms prepared from these formulations in admixture with synergists.
  • Synergists are compounds which increase the effect of the active ingredients without the added synergist itself having to be active.
  • the active compounds according to the invention may furthermore, when used as insecticides in their commercial formulations and in the forms of use prepared from these formulations, be present in mixtures with inhibitors which reduce degradation of the active ingredient after application in the environment of the plant, on the surface of plant parts or in plant tissues ,
  • the active substance content of the application forms prepared from the commercial formulations can vary within wide ranges.
  • the active ingredient concentration of the use forms may be from 0.00000001 up to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.
  • the application is done in a custom forms adapted to the application.
  • plants and parts of plants can be treated.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or Crops (including naturally occurring crops).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, by way of example leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and parts of plants with the active ingredients takes place directly or by acting on their environment, habitat or storage space according to the usual treatment methods, eg by dipping, spraying, evaporating, atomizing, spreading, brushing, injecting and in propagation material, in particular in seed, furthermore by single or multi-layer wrapping.
  • all plants and their parts can be treated.
  • wild-type or plant species obtained by conventional biological breeding methods such as crossing or protoplast fusion, and plant cultivars and their parts are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the terms “parts” or “parts of plants” or “plant parts” have been explained above.
  • Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes and genotypes.
  • the treatment according to the invention may also give rise to superadditive ("synergistic") effects.
  • superadditive for example, reduced application rates and / or enhancements of the spectrum of action and / or an increase in the effect of the substances and agents that can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the actual expected effects.
  • the preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits").
  • traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products.
  • Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances.
  • transgenic plants are the important crops such as cereals (wheat, rice), corn, soybeans, potatoes, sugar beets, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and Grapes), with special emphasis on maize, soya, potato, cotton, tobacco and oilseed rape.
  • Traits which are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins produced in the plants, in particular those produced by the genetic material from Bacillus thuringiensis (eg by the genes CrylA (a) , CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) in the plants (hereinafter "Bt plants”). Traits also highlight the increased resistance of plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene).
  • the genes which confer the desired properties (“traits") can also occur in combinations with one another in the transgenic plants.
  • Examples of “Bt plants” are maize varieties, cotton varieties, soybean varieties and potato varieties which are sold under the trade names YIELD GARD® (eg corn, cotton, soya), KnockOut® (eg maize), StarLink® (eg maize), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), ⁇ ® (tolerance against imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
  • Roundup Ready® tolerance to glyphosate eg corn, cotton, soy
  • Liberty Link® tolerance to phosphinotricin, eg rapeseed
  • ⁇ ® tolerance against imidazolinone
  • STS® tolerance to sulfonylureas eg corn
  • Clearfield® varieties eg corn
  • the listed plants can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active substance mixtures according to the invention.
  • the preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text.
  • the active compounds of the invention not only against plant, hygiene and storage pests, but also in the veterinary sector against animal parasites (ecto- and endoparasites) such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice , Hair pieces, featherlings and fleas.
  • animal parasites ecto- and endoparasites
  • ecto- and endoparasites such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice , Hair pieces, featherlings and fleas.
  • parasites include: From the order of the Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
  • siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
  • heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
  • Actinedida Prostigmata
  • Acaridida Acaridida
  • eg Acarapis spp. Cheyletiella spp., Ornitrocheyletia Spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp.
  • the active compounds of the formula (I) are also suitable for controlling arthropods, the livestock, such as cattle, sheep , Goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, put en, ducks, geese, bees, other pets such as dogs, cats, caged birds, aquarium fish and so-called experimental animals, such as hamsters, guinea pigs, rats and mice infested.
  • livestock such as cattle, sheep , Goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, put en, ducks, geese, bees, other pets such as dogs, cats, caged birds, aquarium fish and so-called experimental animals, such as hamsters, guinea pigs, rats and mice infested.
  • the use of the active compounds according to the invention is carried out in the veterinary sector and in animal husbandry in a known manner by enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boluses, the feed-through procedure, suppositories, by parenteral administration, as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying, pouring (pour-on and spot-on ), washing, powdering and with the aid of active substance-containing moldings, such as collars, ear tags, tail marks, limb bands, holsters, marking devices, etc.
  • enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boluses, the feed-through procedure, suppositories
  • parenteral administration as
  • the active compounds of the formula (I) as formulations (For example, powders, emulsions, flowable agents) containing the active ingredients in an amount of 1 to 80 wt %, apply directly or after 100 to 10 000 dilutions, or use as a chemical bath.
  • the compounds according to the invention exhibit a high insecticidal activity against insects which destroy industrial materials.
  • insects By way of example and preferably without limiting however, the following insects are mentioned: Beetles such as Hylotrupes b Camillus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Emobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus;
  • Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;
  • Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus; Bristle tails like Lepisma saccharina.
  • Non-living materials such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
  • the ready-to-use agents may optionally contain further insecticides and optionally one or more fungicides.
  • the compounds according to the invention can be used to protect against fouling of objects, in particular hulls, sieves, nets, structures, quay systems and signal systems, which come into contact with seawater or brackish water.
  • the compounds according to the invention can be used alone or in combinations with other active substances as antifouling agents.
  • the active substances are also suitable for controlling animal pests in household, hygiene and storage protection, in particular of insects, arachnids and mites, which are used in enclosed spaces, such as, for example, apartments, factory halls, offices, vehicle cabins and the like. occurrence. They can be used to control these pests, alone or in combination with other active ingredients and adjuvants in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include: From the order of Sco ⁇ ionidea eg Buthus occitanus.
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Araneae e.g. Aviculariidae, Araneidae.
  • Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
  • Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
  • siphonaptera e.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • Heteroptera e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
  • Benzoxazinones of formula (II) are known (e.g., WO2007 / 144100) or can be prepared by known methods.
  • Anilines of formula (III) are known (e.g., WO2007 / 144100) or can be prepared by known methods.
  • the compounds of the formula (I) can be obtained, for example the following compounds of the formula (I):
  • the calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values by means of the retention times by linear interpolation between two consecutive alkanones).
  • the lambda-maX values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • the MH + signals were determined with an Agilent MSD system with ESI and positive or negative ionization. NMR spectra were determined on a Bruker Avance 400 equipped with a 60 ⁇ volume flowhead probe.
  • the solvent used was d6-DMSO, tetramethylsilane (0.00 ppm) being used as reference.
  • the examples in the above table were taken up in d 6 -DMSO as a solvent except for Example No. 39 (DMF), No. 51 (CDC1 3 ) and No. 69, which was taken up in CD 3 CN as a solvent.
  • the measurement temperature is 303K if d 6 -DMSO is used as solvent and 298K if CD 3 CN is used as solvent.
  • the samples were determined with a Bruker Avance II 600 or III 600.
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
  • active compound preparation 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Chinese cabbage leaf discs (Brassica pekinensis) infested with all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.
  • Example 2 the following compounds of the preparation examples effect of 90% at a rate of 100g / ha: 1, 7, 14, 20, 32, 44, 65, 97, 153, 193, 224, 231, 236 In this test, for.
  • Example 2 Example 2
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
  • dimethylformamide emulsifier 1.5 parts by weight of dimethylformamide emulsifier: 0.5 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm ⁇ Spodoptera frugiperda).
  • Boophilus microplus test (BOOPMI injection)
  • the drug solution is injected into the abdomen (Boophilus microplus), the animals are transferred to trays and stored in an air-conditioned room.
  • the effect is determined in%.
  • the effect control takes place on storage of fertile eggs. 100% means that no ticks have laid fertile eggs.
  • the following compounds of the preparation examples show an effect of 100% at an application rate of 20 ⁇ g / animal: 24, 26, 27, 30, 31, 33, 36, 37, 38, 40, 42, 43, 44, 65 , 69
  • Vessels containing horsemeat treated with the preparation of active compound of the desired concentration are populated with about 20 Lucilla cuprina larvae.
  • the kill is determined in%. 100% means that all larvae have been killed; 0% means that no larvae have been killed.
  • the following compounds of the preparation examples show an effect of 100% at an application rate of 100 ppm: 24, 26, 27, 30, 31, 33, 36, 37, 38, 40, 42, 43, 44, 65, 69
  • Vessels containing a sponge treated with the preparation of active compound of the desired concentration are mated with Musca domestica adult.
  • the kill is determined in%. 100% means that all flies have been killed; 0% means that no flies have been killed.
  • the following compounds of the preparation examples an effect of 80% at an application rate of 100 ppm: 26, 36, 37
  • Phaedon cochleariae test (PHAECO spray treatment)
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
  • the effect is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm (Spodoptera frugiperda). After the desired time, the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillar has been killed.
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Chinese cabbage leaf discs (Brassica pekinensis) infested with all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration. After the desired time, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.

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  • Organic Chemistry (AREA)
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Abstract

L'invention concerne de nouveaux dérivés de diamide d'acide anthranilique représentés par la formule générale (I) dans laquelle R1, R2, R3, R4, R5, R6, A, Q et n ont les significations données dans le descriptif, leur utilisation comme insecticides et acaricides pour la lutte contre des animaux parasites, également en combinaison avec d'autres agents pour l'augmentation de l'effet, et plusieurs procédés pour la fabrication des dérivés selon l'invention.
PCT/EP2011/059692 2010-06-15 2011-06-10 Dérivés de diamide d'acide anthranilique à chaînes latérales cycliques WO2011157651A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP11726115.6A EP2582695B1 (fr) 2010-06-15 2011-06-10 Dérivés d'acide anthranilique dotés de chaînes latérales cycliques
CN201180038310.7A CN103249729B (zh) 2010-06-15 2011-06-10 具有环状侧链的邻甲酰胺基苯甲酰胺衍生物
KR1020137000990A KR20130112864A (ko) 2010-06-15 2011-06-10 사이클릭 측쇄를 가지는 안트라닐산 디아미드 유도체
ES11726115.6T ES2554903T3 (es) 2010-06-15 2011-06-10 Derivados de diamida de ácido antranílico con cadenas laterales cíclicas
BR112012032238A BR112012032238A2 (pt) 2010-06-15 2011-06-10 derivados de diamida antranílica que têm cadeias laterais cíclicas
JP2013514657A JP6046035B2 (ja) 2010-06-15 2011-06-10 環状側鎖を有するアントラニル酸ジアミド誘導体
MX2012014574A MX2012014574A (es) 2010-06-15 2011-06-10 Derivados diamidoantranilicos que tienen cadenas laterales ciclicas.

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US35489910P 2010-06-15 2010-06-15
EP10166063 2010-06-15
US61/354,899 2010-06-15
EP10166063.7 2010-06-15

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US (1) US8791143B2 (fr)
EP (1) EP2582695B1 (fr)
JP (1) JP6046035B2 (fr)
KR (1) KR20130112864A (fr)
CN (1) CN103249729B (fr)
BR (1) BR112012032238A2 (fr)
ES (1) ES2554903T3 (fr)
MX (1) MX2012014574A (fr)
WO (1) WO2011157651A1 (fr)

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WO2013092519A1 (fr) * 2011-12-19 2013-06-27 Bayer Cropscience Ag Utilisation de dérivés de diamide d'acide anthranilique pour lutter contre les organismes nuisibles dans des cultures transgéniques
JP2013528634A (ja) * 2010-06-18 2013-07-11 バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー 殺虫特性及び殺ダニ特性を有する活性物質組合せ
US9609868B2 (en) 2013-03-06 2017-04-04 Bayer Cropscience Ag Alkoximino-substituted anthranilic acid diamides as pesticides
JP2018027964A (ja) * 2012-02-07 2018-02-22 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ 置換アントラニル酸誘導体を製造する方法
WO2019123194A1 (fr) 2017-12-20 2019-06-27 Pi Industries Ltd. Anthranilamides, leur utilisation en tant qu'insecticides et leurs procédés de préparation
WO2019123195A1 (fr) 2017-12-20 2019-06-27 Pi Industries Ltd. Pyrazolopyridine-diamides, leur utilisation en tant qu'insecticide et leurs procédés de préparation
WO2019150220A1 (fr) 2018-01-30 2019-08-08 Pi Industries Ltd. Nouveaux anthranilamides, leur utilisation en tant qu'insecticides et leurs procédés de préparation

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DE102006032168A1 (de) 2006-06-13 2007-12-20 Bayer Cropscience Ag Anthranilsäurediamid-Derivate mit heteroaromatischen Substituenten
EP2595486A2 (fr) * 2010-07-20 2013-05-29 Bayer Intellectual Property GmbH Utilisation de dérivés d'amide d'acide anthranilique pour lutter contre des insectes et des tétranyques par arrosage, mélange avec le sol, traitement de sillons, application goutte-à-goutte, injection dans le sol, dans le tronc ou dans les fleurs, dans des systèmes hydroponiques, par traitement de trous de plantation ou immersion, application sous forme flottante ou au moyen de boîtes de semences ou par traitement de semences, et pour augmenter la tolérance des plantes au stress abiotique
EP2606732A1 (fr) 2011-12-19 2013-06-26 Bayer CropScience AG Utilisation de dérivés de diamide anthranilique avec des substituants hétéro-aromatiques et hétérocycliques en combinaison avec un agent de contrôle biologique
WO2016070562A1 (fr) * 2014-11-05 2016-05-12 江苏中旗作物保护股份有限公司 Composé diamide anthranilique et son utilisation
CN105254625B (zh) * 2015-11-06 2018-07-27 青岛科技大学 一种含氯代噻唑基苯甲酰胺类化合物及其应用
CN105777713A (zh) * 2016-04-06 2016-07-20 武汉工程大学 N-(2-吡啶基)-2-(2,4-二甲基吡唑甲酰胺基)苯甲酰胺及其制备和用途
CN114716408A (zh) * 2022-03-23 2022-07-08 南开大学 一类含芳香酰胺的双酰胺类衍生物及其制备方法和应用

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JP2013528634A (ja) * 2010-06-18 2013-07-11 バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー 殺虫特性及び殺ダニ特性を有する活性物質組合せ
WO2013092519A1 (fr) * 2011-12-19 2013-06-27 Bayer Cropscience Ag Utilisation de dérivés de diamide d'acide anthranilique pour lutter contre les organismes nuisibles dans des cultures transgéniques
CN104270946A (zh) * 2011-12-19 2015-01-07 拜耳农作物科学股份公司 邻氨基苯甲酸二酰胺衍生物用于防治转基因作物中的害虫的用途
US9414595B2 (en) 2011-12-19 2016-08-16 Bayer Cropscience Ag Use of anthranilic acid diamide derivatives for pest control in transgenic crops
CN104270946B (zh) * 2011-12-19 2017-05-10 拜耳农作物科学股份公司 邻氨基苯甲酸二酰胺衍生物用于防治转基因作物中的害虫的用途
JP2018027964A (ja) * 2012-02-07 2018-02-22 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ 置換アントラニル酸誘導体を製造する方法
US9609868B2 (en) 2013-03-06 2017-04-04 Bayer Cropscience Ag Alkoximino-substituted anthranilic acid diamides as pesticides
WO2019123194A1 (fr) 2017-12-20 2019-06-27 Pi Industries Ltd. Anthranilamides, leur utilisation en tant qu'insecticides et leurs procédés de préparation
WO2019123195A1 (fr) 2017-12-20 2019-06-27 Pi Industries Ltd. Pyrazolopyridine-diamides, leur utilisation en tant qu'insecticide et leurs procédés de préparation
US12024510B2 (en) 2017-12-20 2024-07-02 Pi Industries Ltd. Pyrazolopyridine-diamides, their use as insecticide and processes for preparing the same
WO2019150220A1 (fr) 2018-01-30 2019-08-08 Pi Industries Ltd. Nouveaux anthranilamides, leur utilisation en tant qu'insecticides et leurs procédés de préparation

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US8791143B2 (en) 2014-07-29
BR112012032238A2 (pt) 2015-09-15
JP6046035B2 (ja) 2016-12-14
CN103249729B (zh) 2017-04-05
EP2582695B1 (fr) 2015-09-30
ES2554903T3 (es) 2015-12-28
KR20130112864A (ko) 2013-10-14
JP2013534916A (ja) 2013-09-09
CN103249729A (zh) 2013-08-14
US20120010249A1 (en) 2012-01-12
EP2582695A1 (fr) 2013-04-24

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